
Holiday rentals with a pool in Kiawah Island
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Top-rated rentals with a pool in Kiawah Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Kiawah Island rentals with a pool
House rentals with a pool

Red Sunset Sanctuary Private Heated Pool
Wow! The location was perfect. We were on a family vacation with all ages celebrating my FIL’s service on the USS Yorktown. The closeness to Charleston AND the beach met all our needs, and then some! Highly recommend ~

Private Entrance Suite w/ pool, 5 min from beach
My husband and I enjoyed our stay. The location is in a very nice neighborhood and very close to lots of Charleston's favorite things to do. Liz was a great host giving specific directions as well as checking in to make sure we had everything we needed. However, we did not need to request anything additional than what was provided. Check in and check out was an easy process. We will stay here again.

The Hampton House
This is a nice house with a lot of really great perks. The golf cart, kayaks, fishing rods, beach equipment, and more made it easy to enjoy the week. The location is peaceful and ideal for fishing but not perfect for swimming or waves; we went to adjacent Hunting Island State Park for the kids to ride waves (a state park pass is included by the host). We enjoyed our week!

The Villa Pairidaeza - New Build With Pool
This is our second time staying at this house and we enjoyed every minute of it. The house is very well equipped with all the amenities you can think of. Our big family is definitely coming back for another stay. Thank you!!

Short Stays! Modern 3BD w/ Private Pool
We had a wonderful experience during our recent stay at this Airbnb. The host was exceptionally accommodating, ensuring a smooth check-in process and providing helpful local tips. The thoughtful touches, from a well-equipped kitchen to extra blankets, made us feel right at home. Communication with the host was prompt and friendly, enhancing the overall positive impression

Gorgeous home one block from beach w/ heated pool
It’s a beautiful, well appointed, clean and tastefully decorated home. The home is spacious with a great floor plan. We were 3 families. 6 adults and 5 children. The kids loved the pool. There were numerous pool toys to keep them entertained. The kitchen is a cook’s dream. Everything ( except a coffee grinder) was available. The long kitchen table easily accommodates 12. We enjoyed the porches. There are 3 but we did not use top balcony. ( that is where the fire pit is ) There are lots of steps, but the convenience of the elevator was wonderful. It was a great location as well. We had a lovely time.

Sunset Paradise - Great Location on Island
Great host. Great place to stay.

303 D Port O Call by AvantStay | Oceanfront Condo!
Great stay! We had a wonderful time at this beautiful condo. It was very clean and very well stocked. Our favorite was the view sitting out on the screened in porch. We would definitely stay here again. Look forward to our next visit!
Apartment rentals with a pool

Beach condo with pool and stunning nature views
Loved our stay here. Condo very clean and comfortable, especially beds. Very communicative hosts Thank you for letting us stay

On the Beach-End Unit! Enjoy Dolphins & Sunsets!
Pelican Watch is a beautiful place on Seabrook. The beach is a 2 minute walk from the backdoor with a great view from the back porch. You need a car to get to most restaurants but great places are 10-20 minutes away. Harris Teeter is well stocked nearby with great steaks and seafood as well as wine. I’d definitely stay here again.

Newly renovated Oceanfront Condo ~ Isle of Palms
Elizabeth responded quickly to questions. She is friendly and goes out of her way to make you feel welcome. We enjoyed her condo so much we extended our stay. The condo itself was very clean and exactly as advertised. Very close to private pier and beach. Was nice to go to the beach without the crowds of public beaches. Very close to Patriotic Point, Forts Sumpter and Moultrie. Many restaurants within walking distance. We hope to make it back next year!

Ocean Front Resort Villa
We could not ask for a better host. Patty provided everything we needed and more. She is so friendly, helpful and accommodating. She truly goes above and beyond to ensure the best stay possible. I have stayed here multiple times and hope to stay again in the future. I would absolutely recommend staying here.

HHBT Resort-OceanView-Remodeled-Steps to beach/bar
I’ve stayed at this resort multiple times but this room is by far the best! It was clean, had every thing we needed & more, and was a perfect location for a wagon haul to the beach. It was impressively stocked with things you may forget. We had a wonderful stay & will be staying in this room again for our next stay. Thank you!

Ocean Views at Villamare with Best Pools on HHI!
Had a fabulous stay at Mike and Rachel’s home. Love the location, especially that it was on the beach especially since we have children. The unit was spacious, clean and just as described. Had plenty of games and TVs in all rooms for watching shows or movies. Parking was very convenient and fit our mid size suv under the covered garage area right by elevator to our unit. Overall great experience and would be glad to come back soon! Denis, Olivia O.

Oceanfront Luxury! KING BED 65"TVs Pickleball BAR!
Condo was super easy to get to on the first floor and definitely oceanfront. Although we were on the first floor, we could still see 98% of the ocean over the dunes and easily hear the waves crashing from the balcony. We got to see a family of rabbits hopping through the dune grasses and 99.9% of the time no one is seen between our balcony and the ocean… giving the feeling of seclusion in a populated area. Everything worked as it should in every room in the condo… fantastic TVs, extremely good shower heads, sturdy beach chairs, stout beach umbrella w/ anchor, comfortable plush leather sofa, and a very comfy form fitting memory foam king bed with plenty of pillows for even the finicky sleeper. 99% of my kitchen needs were met…i’ll remember the cooking spray next time. The plush white sand was a pleasant surprise as well as how level and firm the sand gets when the tide goes out, great for bocce ball! BTW, just about any kind of tent, wind shade or popup is allowed on the beach.

Resort Privileges!Pristine!Great location!
Melinda’s condo was perfect for our long weekend stay. It’s in a great location and was very clean. Melinda was a great host and supplied us with terrific information.
Quick stats about holiday rentals with a pool in Kiawah Island
Total rentals
300 properties
Nightly prices starting at
₹12,985 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
280 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
250 properties have a dedicated workspace
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- Hunting Island State Park Beach
- Sullivan's Island Beach
- Palmetto Dunes Oceanfront Resort
- Middleton Place
- Hampton Park
- The Golf Club at Wescott Plantation
- James Island County Park
- Dolphin Head Golf Club
- The Charleston Museum
- Harbor Island Beach
- Yeamans Hall Club
- Shem Creek Park
- Angel Oak Tree
- Waterfront Park
- Bradley Beach
- Bull Point Beach
- Secession Golf Club
- Islanders Beach Park
- Seabrook Beach
- Gibbes Museum of Art
- White Point Garden
- Morris Island Lighthouse
- Isle of Palms Beach
- Hunting Island Beach